Granted Patent
B2
US 12,338,383 · App. 17/550,631 · Granted Jun 24, 2025
3D-printed polyrotaxane additives and compositions
Inventors:
Hasmukh A. Patel (Katy, TX); Ali Z. Khater (Houston, TX); Peter Boul (Houston, TX); Pulickel M. Ajayan (Houston, TX); Muhammad M. Rahman (Houston, TX)
Assignee:
Saudi Arabian Oil Company
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Abstract
This document relates to sealant compositions containing a sliding-ring polymer (polyrotaxane) additive and a polymeric matrix material. The sealant materials exhibit enhanced mechanical properties as compared to the same sealant composition that does not contain the additive. This document also relates to 3D-printed sealant compositions containing a sliding-ring polymer (polyrotaxane) additive and a polymeric matrix material.
Claims (30)
1. A sealant composition comprising:
about 65 wt % to about 95 wt % of a UV-cured epoxy resin;
about 5 wt % to about 20 wt % of a fumed silica; and
about 1 wt % to about 7.5 wt % of a sliding-ring polymer additive comprising at least two molecules of a polyrotaxane selected from the group consisting of an acrylate-terminated polyrotaxane and a cross-linked polyrotaxane bead, wherein the polyrotaxane comprises:
a linear polymer;
at least one ring compound, wherein the linear polymer is threaded through the opening of the ring compound; and
stopper groups disposed at both end terminals of the linear polymer;
wherein the cross-linked polyrotaxane bead is surface-functionalized with epoxide rings; and
wherein the sealant composition exhibits improved tensile strength as compared to the same composition without the sliding-ring polymer additive.
2. The sealant composition of claim 1 , wherein the UV-cured epoxy resin is present in an amount of about 65 wt % to about 90 wt %, about 75 wt % to about 85 wt %, or about 80 wt % to about 85 wt % of the sealant composition.
3. The sealant composition of claim 1 , wherein the sliding-ring polymer additive is an acrylate-terminated polyrotaxane.
4. The sealant composition of claim 1 , wherein the sliding-ring polymer additive is cross-linked polyrotaxane beads, wherein the cross-linked polyrotaxane beads are surface-functionalized with epoxide rings.
5. The sealant composition of claim 1 , wherein the sliding-ring polymer additive is present in an amount of about 1 wt % to about 5 wt % of the sealant composition.
6. The sealant composition of claim 1 , wherein the sealant composition is able to be 3D-printed.
7. The sealant composition of claim 1 , wherein the sealant composition exhibits increased strain tolerance- or flexural strain as compared to the same sealant composition without the sliding-ring polymer additive.
8. A method for preparing a 3D-printed sealant composition, the method comprising:
3D-printing the sealant composition of claim 1 .
9. A method for enhancing the mechanical properties of a sealant composition, the method comprising preparing the sealant composition of claim 1 .
10. The sealant composition of claim 1 , wherein the sealant composition comprises:
about 75 wt % to about 90 wt % of the UV-cured epoxy resin;
about 10 wt % to about 20 wt % of the fumed silica; and
about 1 wt % to about 5 wt % of the cross-linked polyrotaxane bead.
11. The sealant composition of claim 1 , wherein the sealant composition comprises:
about 80 wt % to about 90 wt % of the UV-cured epoxy resin;
about 10 wt % to about 20 wt % of the fumed silica; and
about 1 wt % to about 2.5 wt % of the cross-linked polyrotaxane bead.
12. The sealant composition of claim 1 , wherein the sealant composition comprises:
about 85 wt % the UV-cured epoxy resin;
about 15 wt % of the fumed silica; and
about 2.5 wt % of the cross-linked polyrotaxane bead.
Assignments (5)
CORRECTIVE ASSIGNMENT TO CORRECT THE 1ST INVENTOR'S NAME PREVIOUSLY RECORDED ON REEL 58468 FRAME 106. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT.
Recorded Feb 20, 2025
From: KHATER, ALI Z.; AJAYAN, PULICKEL M.; RAHMAN, MUHAMMAD M.
To: WILLIAM MARSH RICE UNIVERSITY
Reel/Frame 070292/0402 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Jun 1, 2022
From: ARAMCO SERVICES COMPANY
To: SAUDI ARAMCO UPSTREAM TECHNOLOGY COMPANY
Reel/Frame 060066/0887 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Jun 1, 2022
From: SAUDI ARAMCO UPSTREAM TECHNOLOGY COMPANY
To: SAUDI ARABIAN OIL COMPANY
Reel/Frame 060067/0052 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Dec 23, 2021
From: PATEL, HASMUKH A.; BOUL, PETER
To: ARAMCO SERVICES COMPANY
Reel/Frame 058468/0100 →
ASSIGNMENT OF ASSIGNOR'S INTEREST
Recorded Dec 23, 2021
From: KHATER, ALI ZEIN; AJAYAN, PULICKEL M.; RAHMAN, MUHAMMAD M.
To: WILLIAM MARSH RICE UNIVERSITY
Reel/Frame 058468/0106 →
Continuity (1)
References Cited (282)
US 1811799A
· Lukens
· 1931
[cited by applicant]
US 2705050A
· Davis et al.
· 1955
[cited by applicant]
US 3301797A
· Drucket et al.
· 1967
[cited by applicant]
US 3481903A
· Alelio
· 1969
[cited by applicant]
US 3887009A
· Miller et al.
· 1975
[cited by applicant]
US 3938594A
· Rhudy et al.
· 1976
[cited by applicant]
US 4137182A
· Golinkin
· 1979
[cited by applicant]
US 4272430A
· Pieh et al.
· 1981
[cited by applicant]
US 4615809A
· King
· 1986
[cited by applicant]
US 4771112A
· Engelbrecht
· 1988
[cited by applicant]
US 4797433A
· Lahalih
· 1989
[cited by applicant]
US 4883126A
· Leland
· 1989
[cited by applicant]
US 5007481A
· Williams et al.
· 1991
[cited by applicant]
US 5062897A
· Katsunnata
· 1991
[cited by applicant]
US 5159828A
· Steiger
· 1992
[cited by applicant]
US 5352290A
· Takeshita et al.
· 1994
[cited by applicant]
US 5401312A
· Hanst
· 1995
[cited by applicant]
US 5645637A
· Yaniv
· 1997
[cited by applicant]
US 5891983A
· Albrecht
· 1999
[cited by applicant]
US 6089318A
· Laramay et al.
· 2000
[cited by applicant]
US 6324916B1
· Jessop
· 2001
[cited by applicant]
US 6609067B2
· Tare
· 2003
[cited by applicant]
US 6664215B1
· Tomlinson
· 2003
[cited by applicant]
US 6668927B1
· Chatterji et al.
· 2003
[cited by applicant]
US 6828378B2
· Okumura et al.
· 2004
[cited by applicant]
US 6844852B1
· Simons
· 2005
[cited by applicant]
US 7077199B2
· Vinegar et al.
· 2006
[cited by applicant]
US 7497258B2
· Savery et al.
· 2009
[cited by applicant]
US 7523784B2
· Lewis et al.
· 2009
[cited by applicant]
US 7525872B2
· Tang et al.
· 2009
[cited by applicant]
US 7527098B2
· Santra et al.
· 2009
[cited by applicant]
US 7555414B2
· Calhoun
· 2009
[cited by applicant]
US 7612142B2
· Ito et al.
· 2009
[cited by applicant]
US 7622527B2
· Ito et al.
· 2009
[cited by applicant]
US 7637319B2
· Savery et al.
· 2009
[cited by applicant]
US 7654326B1
· Santra et al.
· 2010
[cited by applicant]
US 7773454B2
· Barolak et al.
· 2010
[cited by applicant]
US 7787327B2
· Tang et al.
· 2010
[cited by applicant]
US 7799867B2
· Ito et al.
· 2010
[cited by applicant]
US 7833344B2
· Santra et al.
· 2010
[cited by applicant]
US 7847049B2
· Ito et al.
· 2010
[cited by applicant]
US 7893011B2
· Lewis et al.
· 2011
[cited by applicant]
US 7893168B2
· Ito et al.
· 2011
[cited by applicant]
US 7943718B2
· Ito et al.
· 2011
[cited by applicant]
US 7981943B2
· Ito et al.
· 2011
[cited by applicant]
US 8007911B2
· Ito et al.
· 2011
[cited by applicant]
US 8017688B2
· Ito et al.
· 2011
[cited by applicant]
US 8124569B2
· Khan et al.
· 2012
[cited by applicant]
US 8142562B2
· Klettke et al.
· 2012
[cited by applicant]
US 8309498B2
· Funkhouser et al.
· 2012
[cited by applicant]
US 8382476B2
· Schulte et al.
· 2013
[cited by applicant]
US 8418763B1
· Deen et al.
· 2013
[cited by applicant]
US 8450252B2
· Funkhouser et al.
· 2013
[cited by applicant]
US 8450415B2
· Ito et al.
· 2013
[cited by applicant]
US 8580906B2
· Hayashi et al.
· 2013
[cited by applicant]
US 8587493B2
· Dickey et al.
· 2013
[cited by applicant]
US 8673364B2
· Jalota et al.
· 2014
[cited by applicant]
US 8770038B2
· Secq
· 2014
[cited by applicant]
US 8899331B2
· Burnham
· 2014
[cited by applicant]
US 9023150B2
· Brenneis et al.
· 2015
[cited by applicant]
US 9068051B2
· Yamasaki et al.
· 2015
[cited by applicant]
US 9085487B2
· Silva et al.
· 2015
[cited by applicant]
US 9228993B2
· Shine et al.
· 2016
[cited by applicant]
US 9266972B2
· Yamasaki et al.
· 2016
[cited by applicant]
US 9375699B2
· Ladet
· 2016
[cited by applicant]
US 9428682B2
· Muthusamy et al.
· 2016
[cited by applicant]
US 9617460B2
· Reddy
· 2017
[cited by applicant]
US 9708869B2
· Sarmah et al.
· 2017
[cited by applicant]
US 20030138398A1
· Okumura et al.
· 2003
[cited by applicant]
US 20060048671A1
· Ong
· 2006
[cited by applicant]
US 20080006410A1
· Looney et al.
· 2008
[cited by applicant]
US 20080156225A1
· Bury
· 2008
[cited by applicant]
US 20080287633A1
· Drumheller
· 2008
[cited by applicant]
US 20090030108A1
· Ito et al.
· 2009
[cited by applicant]
US 20090214871A1
· Fukuda et al.
· 2009
[cited by applicant]
US 20090312491A1
· Ito et al.
· 2009
[cited by applicant]
US 20090312492A1
· Ruslim et al.
· 2009
[cited by applicant]
US 20100006288A1
· Santra et al.
· 2010
[cited by applicant]
US 20120006551A1
· Carman et al.
· 2012
[cited by applicant]
US 20130118740A1
· Sherman et al.
· 2013
[cited by applicant]
US 20140096964A1
· Chakraborty et al.
· 2014
[cited by applicant]
US 20140342531A1
· Tominaga et al.
· 2014
[cited by applicant]
US 20150024122A1
· Wu et al.
· 2015
[cited by applicant]
US 20150033719A1
· Lawrence et al.
· 2015
[cited by applicant]
US 20150057196A1
· Debord et al.
· 2015
[cited by applicant]
US 20150152724A1
· Amendt et al.
· 2015
[cited by applicant]
US 20150198008A1
· Smith et al.
· 2015
[cited by applicant]
US 20160102238A1
· Muthusamy et al.
· 2016
[cited by applicant]
US 20200131396A1
· Kang
· 2020
[cited by examiner]
BR 102018014722
· 2020
[cited by applicant]
CN 104204035
· 2014
[cited by applicant]
CN 107522436
· 2017
[cited by applicant]
CN 109133754
· 2019
[cited by applicant]
CN 112456870
· 2021
[cited by applicant]
EP 0383348
· 1990
[cited by applicant]
EP 2820413
· 2015
[cited by applicant]
EP 3060909
· 2016
[cited by applicant]
JP H10158045
· 1998
[cited by applicant]
JP 2016056308A
· 2016
[cited by examiner]
JP 2016088878
· 2016
[cited by applicant]
JP 6647751
· 2020
[cited by applicant]
WO WO2016053319
· 2016
[cited by applicant]
WO WO2016080674
· 2016
[cited by applicant]
WO WO2019090140
· 2019
[cited by applicant]
WO WO2019147559
· 2019
[cited by applicant]
Toyama et al., JP 2016056308 A machine translation in English used for citation, Apr. 21, 2016. (Year: 2016).
[cited by examiner]
U.S. Appl. No. 16/393,016, filed Apr. 24, 2019, Hakimuddin et al.
[cited by applicant]
U.S. Appl. No. 16/593,820, filed Oct. 4, 2019, Patel et al.
[cited by applicant]
U.S. Appl. No. 16/668,730, filed Oct. 30, 2019, Patel et al.
[cited by applicant]
U.S. Appl. No. 17/107,428, filed Nov. 30, 2020, Hull et al.
[cited by applicant]
U.S. Appl. No. 17/550,653, filed Dec. 14, 2021, Patel et al.
[cited by applicant]
Acquah et al., “Carbon Nanotubes and Graphene as Additives in 3D Printing,” Carbon Nanotubes—Current Progress of Their Polymer Composites, InTech, 2016, 26 pages.
[cited by applicant]
Adhikary et al., “Effects of carbon nanotubes on expanded glass and silica aerogel based lightweight concrete,” Nature, Scientific Reports, Jan. 2021, 11:2104, 11 pages.
[cited by applicant]
Andrew, “Global CO
[cited by applicant]
API, “10B-2, Recommended Practice for Testing Well Cements,” American Petroleum Institute, Apr. 2019, 1-124, RP 10B-2, 124 pages.
[cited by applicant]
Arbad et al., “A Review of Recent Research on Contamination of Oil Well Cement with Oil-Based Drilling Fluid and the Need of New and Accurate Correlations,” ChemEngineering, Apr. 2020, 20 pages.
[cited by applicant]
Ashik et al., “A review on methane transformation to hydrogen and nanocarbon: Relevance of catalyst characteristics and experimental parameters on yield,” Renewable and Sustainable Energy Reviews, Sep. 2017, 76:743-767,…
[cited by applicant]
asmi.jp [online], “SeRM Series Products List,” asmi.jp, Advanced Softmaterials Inc., retrieved from URL <www.asmi.jp/en/product#sec_03>, retrieved on Aug. 15, 2019, available on or before Jan. 2013 (via wayback machine …
[cited by applicant]
Bagheri et al., “Rubber-Toughened Epoxies: A Critical Review,” Polym. Rev., 2009, 49:201-225, 26 pages.
[cited by applicant]
Bett, “Geothermal Well Cementing, Materials and Placement Techniques,” United Nations University, Geothermal Training Programme, Reports 2010, No. 10, 2010, 32 pages.
[cited by applicant]
Brichni et al., “Optimisation of Magnesium Oxychloride Cement Properties by Silica Glass,” Adv. Cem. Res., Jul. 2016, 28:10 (654-663), 10 pages.
[cited by applicant]
Bruns and Stoddart, “The Nature of the Mechanical Bond: from molecules to machines,” Wiley, 2017, 786 pages.
[cited by applicant]
Buchanan et al., “Metal 3D printing in construction: A review of methods, research, applications, opportunities and challenges,” Engineering Structures, Feb. 2019, 180:332-348, 36 pages.
[cited by applicant]
Cao et al., “Study of the in-situ growth of carbon nanofibers on cement clinker,” Mater. Res. Express, May 2020, 7:5 (055306), 10 pages.
[cited by applicant]
Capper et al., “Internal antiplasticisation in highly crosslinked amine cured multifunctional epoxy resins,” Polymer, 2018, 146:321-330, 11 pages.
[cited by applicant]
Carey et al., “Fracture-permeability behavior of shale,” Journal of Unconventional Oil and Gas Resources, Sep. 2015, 11, 53 pages.
[cited by applicant]
Chambers et al., “Liquid crystal elastomer-nanoparticle systems for actuation,” Journal of Materials Chemistry, 2009, 19.11:1524-1531, 7 pages.
[cited by applicant]
Chatham et al., “A review of the process physics and material screening methods for polymer powder bed fusion additive manufacturing,” Progress in Polymer Science, Jun. 2019, 93:68-95, 28 pages.
[cited by applicant]
Chen et al., “Enhancement of mechanical and wear resistance performance in hBN reinforced epoxy nanocomposites,” Polym. Int., 2017, 66: 659, 25 pages.
[cited by applicant]
Chen et al., “Rapid control of phase growth by nanoparticles,” Nature Communications, May 2014, 5.1, 9 pages.
[cited by applicant]
Cho et al., “Cell-Encapsulating Hydrogel Puzzle: Polyrotaxane-Based Self-Healing Hydrogels,” Chem. Eur. J., 2019, 26(4):913-920, 22 pages.
[cited by applicant]
Choi et al., “Highly elastic binders integrating polyrotaxanes for silicon microparticle anodes in lithium ion batteries,” Science, Jul. 2017, 357.6348:279-283, 5 pages.
[cited by applicant]
Cordero et al., “Strengthening of ferrous binder jet 3D printed components through bronze infiltration,” Additive Manufacturing, May 2017, 15:87-92, 6 pages.
[cited by applicant]
Cui et al., “Electrical and mechanical properties of electrically conductive adhesives from epoxy, micro-silver flakes, and nano-hexagonal boron nitride particles after humid and thermal aging,” International Journal of…
[cited by applicant]
Davidson et al., “3D Printable and Reconfigurable Liquid Crystal Elastomers with Light-Induced Shape Memory via Dynamic Bond Exchange,” Advanced Materials, Jan. 2020, 6 pages.
[cited by applicant]
DebRoy et al., “Additive manufacturing of metallic components-process, structure and properties,” Progress in Materials Science, Mar. 2018, 92:112-224, 114 pages.
[cited by applicant]
DebRoy et al., “Scientific, technological and economic issues in metal printing and their solutions,” Nature Materials, Jul. 2019, 18, 7 pages.
[cited by applicant]
Dowling et al., “A review of critical repeatability and reproducibility issues in powder bed fusion,” Materials & Design, Jan. 2020, 186, 18 pages.
[cited by applicant]
El-Wardany et al., “Challenges in three-dimensional printing of high-conductivity copper,” Journal of Electronic Packaging, Jun. 2018, 140.2:020907, 12 pages.
[cited by applicant]
Enayatpour et al., “Advanced Modeling of Cement Displacement Complexities,” SPE/IADC-184702-MS, Society of Petroleum Engineers (SPE), presented at the SPE/IADC Drill Conference and Exhibition, Mar. 2017, 21 pages.
[cited by applicant]
Fayazfar et al., “A critical review of powder-based additive manufacturing of ferrous alloys: Process parameters, microstructure and mechanical properties,” Materials & Design, Apr. 2018, 144:98-128, 31 pages.
[cited by applicant]
Foldyna et al., “Dispersion of carbon nanotubes for application in cement composites,” Science Direct, Procedia Engineering, 2016, 149:94-99, 6 pages.
[cited by applicant]
Funkhouser and Norman, “Synthetic Polymer Fracturing Fluid for High-Temperature Application,” SPE 80236, Society of Petroleum Engineers (SPE), International Symposium on Oilfield Chemistry, Feb. 5-7, 2003, 6 pages.
[cited by applicant]
Gaillard et al., “Novel Associative Acrylamide-based Polymers for Proppant Transport in Hydraulic Fracturing Fluids,” SPE 164072, Society of Petroleum Engineers (SPE), SPE International Symposium on Oilfield Chemistry, …
[cited by applicant]
Gelebart et al., “Photoresponsive fiber array: toward mimicking the collective motion of cilia for transport applications,” Advanced Functional Materials, Aug. 2016, 26.29:5322-5327, 6 pages.
[cited by applicant]
Genedy et al., “Examining epoxy-based nanocomposites in wellbore seal repair for effective CO
[cited by applicant]
Gladman et al., “Biomimetic 4D printing,” Nature Materials, Apr. 2016, 15.4:413-418, 7 pages.
[cited by applicant]
Global Status of CCS Report, Dec. 11, 2020, Global CCS Institute, 44 pages.
[cited by applicant]
Goeppert et al., “Air as the renewable carbon source of the future: an overview of CO
[cited by applicant]
Gojny et al., “Carbon nanotube-reinforced epoxy-composites: enhanced stiffness and fracture toughness at low nanotube content,” Compos. Sci. Technol., 2004, 64:2363-2371, 9 pages.
[cited by applicant]
Gong et al., “Analysis of defect generation in Ti-6Al-4V parts made using powder bed fusion additive manufacturing processes,” Additive Manufacturing, Oct. 2014, 1, 60 pages.
[cited by applicant]
Gorsse et al., “Additive manufacturing of metals: a brief review of the characteristic microstructures and properties of steels, Ti-6A1-4V and high-entropy alloys,” Science and Technology of Advanced Materials, Dec. 201…
[cited by applicant]
Guo et al., “Shape memory epoxy composites with high mechanical performance manufactured by multi-material direct ink writing,” Compos. Part A Appl. Sci. Manuf., 2020, 135: 105903, 8 pages.
[cited by applicant]
Gupta and Carman, “Fracturing Fluid for Extreme Temperature Conditions is Just as Easy as the Rest,” SPE 140176, Society of Petroleum Engineers (SPE), SPE Hydraulic Fracturing Technology Conference, Jan. 24-26, 2011, 5 …
[cited by applicant]
Harada et al., “Preparation and properties of inclusion complexes of polyethylene glycol with α-cyclodextrin,” Macromolecules, 1993, 26:5698-5703, 6 pages.
[cited by applicant]
Harada et al., “Supramolecular polymeric materials via cyclodextrin-guest interactions,” Accounts of Chemical Research, Jul. 2014, 47.7:2128-2140, 13 pages.
[cited by applicant]
Hart et al., “Material properties and applications of mechanically interlocked polymers,” Nat. Rev. Mater., 2021, 6:6 (508-530), 23 pages.
[cited by applicant]
Hepburn et al., “The technological and economic prospects for CO
[cited by applicant]
Herzog et al., “Additive Manufacturing of Metals,” Acta Mater. 2016, 117:371-392, 22 pages.
[cited by applicant]
Hitzler et al., “In-plane anisotropy of selective laser-melted stainless steel: The importance of the rotation angle increment and the limitation window,” Proceedings of the Institution of Mechanical Engineers, Part L: …
[cited by applicant]
Hojjatzadeh et al., “Direct observation of pore formation mechanisms during LPBF additive manufacturing process and high energy density laser welding,” International Journal of Machine Tools and Manufacture 153:103555, …
[cited by applicant]
Houben et al., “Plasticization behavior of crown-ether containing polyimide membranes for the separation of CO
[cited by applicant]
Hoyos-Palacio et al., “Catalytic effect of Fe, Ni, Co and Mo on the CNTs production,” IOP Conference Series: Materials Science and Engineering, 2014, 59:012005, 9 pages.
[cited by applicant]
Huang et al., “Finite element analysis of thermal behavior of metal powder during selective laser melting,” International Journal of Thermal Sciences, Jun. 2016, 104:146-157, 12 pages.
[cited by applicant]
Hull et al., “Chemomechanical Effects of Oxidizer-CO
[cited by applicant]
Hull et al., “Oxidative Kerogen Degradation: A Potential Approach to Hydraulic Fracturing in Unconventionals,” Energy Fuels, 2019, 33: 4758-4766, 8 pages.
[cited by applicant]
Hull et al., “Synthesis and structural characterization of CO
[cited by applicant]
Hur et al., “Reactive force fields for modeling oxidative degradation of organic matter in geological formations,” RSC Adv. 2021, 11:29298-29307, 23 pages.
[cited by applicant]
Isaka et al., “Influence of long-term operation of supercritical carbon dioxide based enhanced geothermal system on mineralogical and microstructurally-induced mechanical alteration of surrounding rock mass,” Renewable …
[cited by applicant]
Isfahani et al., “Dispersion of multi-walled carbon nanotubes and its effects on the properties of cement composites,” Cement and Concrete Composites, Nov. 2016, 74:154-163, 10 pages.
[cited by applicant]
Isobe et al., “Thermally dissociable pseudo-polyrotaxane as a supramolecular shrinkage suppressor for epoxy-amine curing system,” Journal of Polymer Science Part A: Polymer Chemistry, Mar. 2008, 46.6:2305-2308, 4 pages.
[cited by applicant]
Jafariesfad et al., “Cement Sheath Modification Using Nanomaterials for Long-term Zonal Isolation of Oil Wells: Review,” Journal of Petroleum Science and Engineering, 2017, 156:662-672, 28 pages.
[cited by applicant]
Jiang et al., “Highly Stretchable and Instantly Recoverable Slide-Ring Gels Consisting of Enzymatically Synthesized Polyrotaxane with Low Host Coverage,” Chem. Mater., 2018, 30:15 (5013), 10 pages.
[cited by applicant]
Jin et al., “Synthesis and application of epoxy resins: A review,” J. Ind. Eng. Chem., Sep. 2015, 29:1-11, 11 pages.
[cited by applicant]
Kato et al., “Organic-Inorganic Hybrid Slide-Ring Gels: Polyrotaxanes Consisting of Poly(dimethylsiloxane) and γ-Cyclodextrin and Subsequent Topological Cross-Linking,” Macromolecules, Aug. 18, 2009, 42:7129-7136, 8 pag…
[cited by applicant]
Khuenkaew et al., “Resistance spot welding of SUS316L austenitic/SUS425 ferritic stainless steels: weldment characteristics, mechanical properties, phase transformation and solidification,” Metals, Jun. 2019, 9.6, 17 pa…
[cited by applicant]
Kim et al., “Development of CO
[cited by applicant]
Koyanagi et al., “Movable Cross-Linked Polymeric Materials from Bulk Polymerization of Reactive Polyrotaxane Cross-Linker with Acrylate Monomers,” Macromolecules 2017, 50:5695-5700, 6 pages.
[cited by applicant]
Kuo et al., “Bonding behavior of repair material using fly-ash/ground granulated blast furnace slag-based geopolymer,” Materials, Jan. 2019, 12.10, 16 pages.
[cited by applicant]
Ladva et al., “The Cement-to-Formation Interface in Zonal Isolation,” IADC/SPE 88016, Society of Petroleum Engineers (SPE), presented at the IADC/SPE Asia Pacific Drilling Technology Conference and Exhibition in Kuala L…
[cited by applicant]
Levenfeld et al., “Effect of residual carbon on the sintering process of M2 high speed steel parts obtained by a modified metal injection molding process,” Metallurgical and Materials Transactions, Jun. 2002, A:33.6 (18…
[cited by applicant]
Lewis et al., “Direct ink writing of three-dimensional ceramic structures,” Journal of the American Ceramic Society, Dec. 2006, 89.12:3599-3609, 11 pages.
[cited by applicant]
Li et al., “Contamination of Cement Slurries with Diesel-Based Drilling Fluids in a Shale Gas Well,” J. Nat. Gas Sci. Eng., Aug. 2015, 27:1312-1320, 9 pages.
[cited by applicant]
Li et al., “Residual stress in metal additive manufacturing,” Procedia Cirp, Jan. 2018, 71:348-353, 6 pages.
[cited by applicant]
Li et al., “Slide-ring shape memory polymers with movable cross-links,” React. Funct. Polym., 2017, 119:26-36, 25 pages.
[cited by applicant]
Lin et al., “Rapid macroscale shape morphing of 3D-printed polyrotaxane monoliths amplified from pH-controlled nanoscale ring motions,” J. Mater. Chem., 2018, C:6 (11956), 5 pages.
[cited by applicant]
Lin et al., “Ring Shuttling Controls Macroscopic Motion in a Three-Dimensional Printed Polyrotaxane Monolith,” Chem. Int. Ed., 2017, 56:4452-4457, 7 pages.
[cited by applicant]
Liu et al., “A novel method to evaluate cement shale bond strength,” SPE-173802-MS, Society of Petroleum Engineers (SPE), presented at the SPE International Symposium on Oilfield Chemistry, The Woodlands, Texas, Apr. 13…
[cited by applicant]
Liu et al., “Graphene Lubricant,” Applied Materials Today, 2020, 20:2020 (100662), 31 pages.
[cited by applicant]
Luo et al., “A survey of finite element analysis of temperature and thermal stress fields in powder bed fusion additive manufacturing,” Additive Manufacturing, May 2018, 21:318-332, 15 pages.
[cited by applicant]
Mather et al., “Michael addition reactions in macromolecular design for emerging technologies,” Progress in Polymer Science, May 2006, 31.5:487-531, 45 pages.
[cited by applicant]
Mayumi et al., “Structure and dynamics of polyrotaxane and slide-ring materials,” Polymer, 2010, 51:959-967, 9 pages.
[cited by applicant]
Mikhalchan et al., “Aligned carbon nanotube-epoxy composites: the effect of nanotube organization on strength, stiffness, and toughness,” J. Mater. Sci., 2016, 51:10005-10025, 21 pages.
[cited by applicant]
Mostafaei et al., “Binder jet 3D printing—Process parameters, materials, properties, modeling, and challenges,” Progress in Materials Science, Jun. 2021, 119:100707, 141 pages.
[cited by applicant]
Nakahata et al., “Self-Healing Materials Formed by Cross-Linked Polyrotaxanes with Reversible Bonds,” Chem, 2016, 1:5 (766-775), 11 pages.
[cited by applicant]
Nelson and Guillot, “Well Cementing,” Second Edition, Schlumberger, 2006, 807 pages.
[cited by applicant]
Obayi et al., “Effect of grain sizes on mechanical properties and biodegradation behavior of pure iron for cardiovascular stent application,” Biomatter, Jan. 2016, 6.1:e959874, 10 pages.
[cited by applicant]
Ohm et al., “Liquid Crystalline Elastomers as Actuators and Sensors,” Advanced Materials, Aug. 2010, 22: 3366-3387, 22 pages.
[cited by applicant]
Oliveira et al., “Processing parameters in laser powder bed fusion metal additive manufacturing,” Materials & Design, Aug. 2020, 193, 12 pages.
[cited by applicant]
Opedal et al., “Experimental study on the cement-formation bonding,” SPE 168138, Society of Petroleum Engineers (SPE), presented at the SPE International Symposium and Exhibition on Formation Damage Control, Lafayette, …
[cited by applicant]
Peerzada et al., “Additive Manufacturing of Epoxy Resins: Materials, Methods, and Latest Trends,” Ind. Eng. Chem. Res., 2020, 59:14, 52 pages.
[cited by applicant]
Prabhakar et al., “Enhancing the Gel Transition Time and Right-Angle-Set Property of Oil Well Cement Slurries by Incorporating CSA Cement and Gypsum,” IPTC-19224-MS, International Petroleum Technology Conference, Mar. 2…
[cited by applicant]
Prajapati et al., “Measurement of anisotropic thermal conductivity and inter-layer thermal contact resistance in polymer fused deposition modeling (FDM),” Additive Manufacturing, May 2018, 21:84-90, 7 pages.
[cited by applicant]
Pruksawan et al., “Homogeneously Dispersed Polyrotaxane in Epoxy Adhesive and Its Improvement in the Fracture Toughness,” Macromolecules, 2019, 52:2464-2475, 12 pages.
[cited by applicant]
Radonjic and Oyibo, “Experimental evaluation of wellbore cement-formation shear bond strength in presence of drilling fluid contamination,” International Conference on Porous Media and Their Applications in Science, Eng…
[cited by applicant]
Ramsdale-Capper et al., “Internal antiplasticisation in highly crosslinked amine cured multifunctional epoxy resins,” Polymer, Jun. 2018, 146:321-330, 10 pages.
[cited by applicant]
Reddy et al., “Relating Cement Additive Performance to Mix Water Composition for Deep Water and Salt Zone Applications,” SPE-180344-MS, Society of Petroleum Engineers (SPE), SPE Deepwater Drilling and Completions Confer…
[cited by applicant]
Rimdusit et al., “Shape memory polymers from benzoxazine-modified epoxy,” Smart Mater. Struct., 2013, 22:075033, 13 pages.
[cited by applicant]
Roca et al., “Policy needed for additive manufacturing,” Nature Materials, Aug. 2016, 15:8, 4 pages.
[cited by applicant]
Saed et al., “Molecularly-engineered, 4D-Printed liquid crystal elastomer actuators,” Advanced Functional Materials, 2019, 29.3, 9 pages.
[cited by applicant]
Sajadi et al., “Direct ink writing of cement structures modified with nanoscale additive,” Advanced Engineering Materials, Aug. 2019, 21.8:1801380, 10 pages.
[cited by applicant]
Seo et al., “Development of a supramolecular accelerator simultaneously to increase the cross-linking density and ductility of an epoxy resin,” Chem. Eng. J., 2019, 356:303-311, 30 pages.
[cited by applicant]
Seo et al., “Enhanced Mechanical Strength, Flexibility, and Shape-Restoring Rate of a Drug-Eluting Shape-Memory Polymer by Incorporation of Supramolecular Cross-Linkers,” ACS Macro Lett., 2020, 9:389-395, 7 pages.
[cited by applicant]
Simao et al., “Cementing Solutions for Salt- and CO
[cited by applicant]
Singh et al., “Powder bed fusion process in additive manufacturing: An overview,” Materials Today: Proceedings, Jan. 2020, 26:3058-3070, 13 pages.
[cited by applicant]
Snow et al., “Invited Review Article: Review of the formation and impact of flaws in powder bed fusion additive manufacturing,” Additive Manufacturing, Jul. 2020, 15 pages.
[cited by applicant]
Soto et al., “Self-assembly of a supramolecular network with pseudo-rotaxane cross-linking nodes and its transformation into a mechanically locked structure by rotaxane formation,” Chemical Communications, 2016, 52:1414…
[cited by applicant]
Sun et al., “Short-aramid-fiber toughening of epoxy adhesive joint between carbon fiber composites and metal substrates with different surface morphology,” Compos. Part B Eng., 2015, 77:38-45, 30 pages.
[cited by applicant]
Tagliaferri et al., “Direct ink writing of energy materials,” Materials Advances, 2021, 2.2:540-563, 24 pages.
[cited by applicant]
Tao et al., “A Brief Review of Gas Migration in Oilwell Cement Slurries,” Energies, 2021, 14:2369, 22 pages.
[cited by applicant]
Telschow et al., “Cement Formation—A Success Story in a Black Box: High Temperature Phase Formation of Portland Cement Clinker,” Industrial & Engineering Chemistry Research (I&EC Research), American Chemical Society (AC…
[cited by applicant]
Tong et al., “Committed Emissions from Existing Energy Infrastructure Jeopardize 1.5° C. Climate Target,” Nature, 2019, 572:7769 (373-377), 17 pages.
[cited by applicant]
Tran et al., “3D printing of highly pure copper,” Metals, Jul. 2019, 9.7:756, 24 pages.
[cited by applicant]
Ürk et al., “Structure-controlled growth of vertically-aligned carbon nanotube forests using iron-nickel bimetallic catalysts,” Materials Advances, 2021, 2:2021-2030, 10 pages.
[cited by applicant]
Utela et al., “A review of process development steps for new material systems in three dimensional printing (3DP),” Journal of Manufacturing Processes, Jul. 2008, 10.2:96-104, 9 pages.
[cited by applicant]
Vyavahare et al., “Fused deposition modelling: A review,” Rapid Prototyping Journal, Jan. 2020, 26 pages.
[cited by applicant]
Wang et al., “Molecular Simulation of CO
[cited by applicant]
Wang et al., “Relaxation and Reinforcing Effects of Polyrotaxane in an Epoxy Resin Matrix,” Macromolecules, 2006, 39:3 (1046-1052), 7 pages.
[cited by applicant]
Welch et al., “Shear strength and permeability of the cement-casing interface,” International Journal of Greenhouse Gas Control, Apr. 2020, 95, 29 pages.
[cited by applicant]
Wenz et al., “Cyclodextrin Rotaxanes and Polyrotaxanes,” Chem. Rev., 2006, 106:782-817, 36 pages.
[cited by applicant]
Wimpenny et al., “Advances in 3D printing & additive manufacturing technologies,” Singapore: Springer, 2017, 195 pages.
[cited by applicant]
Wu et al., “A Crown Ether-Containing Copolyimide Membrane with Improved Free Volume for CO
[cited by applicant]
Wu et al., “High-strain slide-ring shape-memory polycaprolactone-based polyurethane,” Soft Matter, 2018, 14:4558, 28 pages.
[cited by applicant]
Yakovlev et al., “Modification of Cement Matrix Using Carbon Nanotube Dispersions and Nanosilica,” Science Direct, Procedia Engineering, Modern Building Materials, Structures and Techniques, MBMST 2016, 2017, 172:1261-1…
[cited by applicant]
Zhan et al., “In situ-grown carbon nanotubes enhanced cement-based materials with multifunctionality,” Cement and Concrete Composites, Apr. 2020, 108:103518, 11 pages.
[cited by applicant]
Zhang et al., “Dibenzo-21-crown-7-ether contained 6FDA-based polyimide membrane with improved gas selectivity,” Separation and Purification Technology, 2021, 264:118454, 13 pages.
[cited by applicant]
Zhang et al., “Three-Dimensional Printing of Continuous Flax Fiber-Reinforced Thermoplastic Composites by Five-Axis Machine,” Materials, 2020, 13:1678, 11 pages.
[cited by applicant]
Zoback, “Reservoir geomechanics,” Cambridge University Press, 2010, 2 pages.
[cited by applicant]